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Compare 706 Vacation Homes in Windham with updated reviews, rates, and availability.

"Perfect for a family and friends weekend! Lots of room for everyone to be comfortable!"

Kitchen flows on to outdoor patio, light filled, open views.

"Enjoyed this peaceful home and property. "

"We were two couples (in our 60’s) in Portland for a couple days visiting. John’s place was wonderful! We had plenty of space for the four of us with room to spare. Very comfortable and relaxing. We absolutely LOVED the front porch/deck. Very spacious and an amazing view of the beach and ocean! Bathroom and kitchen were not “updated” but it’s a 110 year old home so we really didn’t mind - everything worked and that’s what’s important. The apartment is upstairs and John lives downstairs. ...

"Just as advertised, would definitely stay here again. Great location!"

"If you need a place to stay in your way to Boston or Acadia, this will work fine. It was clean and newly remodeled. The host is very quickly responsive, but unfortunately was not able to answer our questions. The house has limited cooking supplies and dishes, and wash cloths were not provided. Overall, it was fine for passing through, but not well stocked or ready for an extended stay. "

Walkway around the corner to the beach !

"The picture on VRBO leads you to believe you just go down the pathway shown to get to the beach when you are actually in a neighborhood and have to walk down the street to get to the beach. The house was very clean and both beds were very comfortable. The host was very fast to respond to my messages. Needs clean shower liner. We enjoyed our stay. "

"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"

"Short visit but fun little cottage off the beaten path. Most comfortable beds ever and very responsive host and caretaker. Would stay here again. Loved the nearby waterfront restaurants."

SAR 1,391 total

includes taxes & fees

25 Nov - 26 Nov

"My friends and I stayed for one night in the gorgeous Gregory House. We've stayed here before and absolutely love it! There are so many beautiful details to the house and it's great for larger groups. We love the game room although it's often hard to get us out of the kitchen. Laura has been an amazing host as always! Very responsive, down to earth, and great to work with. We'd love to stay here again."

SAR 4,207 total

includes taxes & fees

29 Nov - 30 Nov

"Beautiful home! Well kept, clean and very comfortable. A little touch of history in this wonderful house and neighborhood. Great location, quick to Portland and the airport. We loved it!!!! Owner communication is a 10+++. "

"Very nice little house. That being said, the house was good for us as we weren’t there much, but if you plan on spending a lot of time in the house it is small, the bathroom is made for small people. I would recommend this listing as the host is very quick to respond and very pleasant and helpful."

"House was great, location was perfect and the local property manager was very responsive and helpful. "

"We really enjoyed this home and the location. The upgrades were beautiful and the restaurants nearby were amazing. When we checked out and took out our trash the outside bin had a lock on it so our only issue was not being able to access that but that wasn’t anyone’s fault. "

SAR 1,591 total

includes taxes & fees

5 Dec - 6 Dec

"We loved staying at the Holt House. It's a truly beautiful building. It's like staying in a hotel from another era. The room was beautifully decorated with victorian decor and we loved it. It was also handy to have access to a full kitchen on the first floor where we washed some of our dishes. Overall, it was a cozy and quiet place to stay."

"This is owners first year renting. It needs a complete review by electrician because there are several outlets not working. We also had trouble with the thermostats and heat. So that needs help too. The 1800 salt box portion of the home was charming to us. The addition added a great number of beds and baths. The kitchen was marginally stocked with bowls, etc so bring your own.. kitchen could have been cleaner too. So not smooth sailing but a comfy no fuss second home"

"The house we stayed in was wonderful. It met all of our expectations. I highly recommend it!"

"We had a wonderful time! Beautiful location.. very comfortable accommodations!! "

"This property is fantastic and I would prioritize staying there each and every time I visit Portland."

"Traveled from New Mexico to visit with my son. I was looking for a place which would be near my son's residence giving us a centralized place to meet. It was just a few minutes away from my son's residence. House served all our needs and was clean and neat. Beautiful views from windows and deck. Will definitely stay again!!!"